Essential Men’s Fall and Winter Travel Apparel

Take a look at our picks for the best travel clothing for men for this Fall and Winter.  Updated for 2017, these will make great gifts for men who are travelling this season.

Men's Fall and Winter Travel Apparel

Disclosure: This article contains affiliate links. That means we earn a commission when you use the links on this site to buy something on Amazon, book a hotel, etc.. You don’t pay anything extra, and it helps us cover our costs. If you’d like to learn more about how this works, you can read more under our Disclaimer page. For more info and limitations, please read our Disclaimer.

Fall and Winter Men’s Apparel Essentials

Alright gentlemen, or ladies shopping for gentlemen, I (Geoff) have put together a list of some cold weather essentials for the traveller. If you’re planning a Fall or Winter trip, your luggage is going to get pretty full pretty quick. Fall and winter clothing is bulky, so you’ll want items that are multi-functional, like a pullover sweater that will look just as good with jeans as it does with dressier pants (trousers for my UK friends). You’ll also want to think in layers, thermal, base and outer depending on where you’re going and how long you’ll be outside for. If the sun comes out, you can take a layer off and still be protected and warm enough. Here is a curated list to help you find the right apparel to take with you.

For the Head & Neck


The North Face® Salty Dog Beanie

One Size, Multiple Colors Available

Geoff’s Pick – I bought this Salty Dog winter hat from the NorthFace store in Vancouver right before a winter trip that took us from Milan to Amsterdam and it was perfect. Looks great, feels very comfortable and it’s very warm!

More Info


Helly Hansen Business Beanie

One Size, Black or Charcoal

All business baby! This men’s winter hat is perfect for those looking for a low-key, classic but functional hat this winter.  Stylish with a double layer wool/polyester blend from a trusted brand that specializes in battling the cold.

More Info


180s Urban Ear Warmers

One Size, Black or Steel Grey

Keep those ears warm, and your hair in place with these ear muffs for men! Collapsable, one-size, fleece. Perfect for business travellers or those who just don’t like wearing hats.

More Info


Levi’s® Men’s Hunter Trapper Hat

Available in s/m or l/xl

Go arctic hunter style this winter and stay extra warm. Not actual fur but it will definitely keep both your head and your ears warm during those long days exploring.

More Info


Columbia Scarf

One size, Available in black or navy

Get fleecy with it and stay extra warm. Plenty of length to wrap around, and best of all, it’s machine washable!

More Info


Veniroc Cashmere Scarf

One size, 70″ x 12″

Wrap up your neck and keep your throat warm on your travels this winter. Extremely soft to help the neck from chaffing and stretchy too which is nice for breathability.

More Info


For the Body


Columbia Cascades Explorer Midweight Fleece

Size: S  M  L  XL

Anti-pilling micro fleece full zip base layer to keep toasty warm.  Also great on its own if it’s not too cold. Looks great, super comfy, zippered pockets, and machine washable. Multiple colour choices available.


ZeroXposur Men’s Block Quilted Puffer Vest

Size: S M L XL

A perfect solution for those crisp late fall days. Keep those arms free! Light weight, machine washable and a great value.


Columbia Men’s Frost Fighter Jacket

Size: S M L XL

Geoff’s Pick – I love how this jacket fits nice and snug, no extra loose material. Zippered pockets, it has a special material around the chin to eliminate that nasty chaffing guys get.  Water resistant, faux-down, awesome!


Dockers Men’s Soft Acrylic Zip Mock

Size: S M L XL

Look great and be comfortable on your fall/winter trips. A great staple to have in our luggage as it looks great with jeans or khakis.


Helly Hansen Men’s Seven J Jacket

Size: S M L XL

Stay completely dry in the wet weather. Water repellant and windproof, very comfortable and also has some nice material around the chin to prevent chaffing. Comes with a hood and storm flap.


Duofold Men’s Mid Weight Varitherm Thermal Pant

Size: S M L XL

You are not going to go on a winter trip without thermal underwear. Long days out exploring the city, or hitting the slopes these are a must have!


ColdPruf Men’s Crew Neck Base Layer

Size: S M L XL

Thermal underwear shouldn’t be limited to the legs. Stay completely warm with a base layer to help you stay out exploring longer!


HANES ComfortSoft Lounge Pants

Size: S M L XL

After a long day you won’t be able to resist sliding these on. Fall and winter are all about coziness and these are perfect for lounging around. Soft waistband, soft cotton, start relaxing!


For the Hands and Feet


3m Thinsulate Thermal Lined Winter Gloves

Size: S/M M/L

Keep those digits toasty warm on you trip this winter. Handsome, snug, knitted with thermal lining on the inside.  I had these for a winer in Prague and they were wonderful.


Columbia Men’s M Thermarator Gloves

Size: S L

Geoff’s Pick – These are my choice because I am always looking at maps or opening information apps on my phone when we’re travelling. The last thing I want to do when it’s cold and windy is take off my gloves so I can find where I’m going!


Dickies 2 Pack Acrylic Thermal Boot Socks

Shoe Size: 6-12

Geoff’s Pick – Warm and soft but not too thick. Wear them with shoes or boots, great quality.  Very comfortable, they come up just over mid-calf.


Spikerking Winter Thermal Hiker Socks

Shoe Size 6-12

Now if you need warmth and style, these are a great choice. Multiple colours, warm, stretchy and they have an elastic band to help hold them up.